Make the puddings In a medium saucepan, combine the wine and sugar and bring to a boil. Simmer over moderately high heat until reduced to 1 cup, about 18 minutes.

In another small saucepan, bring the milk and cream to a boil. In a large bowl, beat the egg yolks. Gradually beat in the hot cream. Add the chocolate and butter; let stand for 2 minutes, then stir until smooth. Stir in half of the wine syrup. Pour the pudding into six 6- to 8-ounce heatproof glass jars or glasses. Refrigerate for at least 2 hours or overnight.

Make the meringue In the bowl of a stand mixer set over a saucepan of simmering water, whisk the egg whites with the sugar and cream of tartar until warm and the sugar is dissolved, 3 to 5 minutes. Let cool slightly. In the mixer, beat the whites at medium-high speed until firm, glossy peaks form, about 2 minutes.

Scrape the meringue into a pastry bag fitted with a large star tip and pipe it onto the puddings. Using a kitchen torch, brown the meringue. Serve with the shortbreads and remaining wine syrup.

For the Shortbreads: Preheat the oven to 350° and line a large baking sheet with parchment paper. In a stand mixer fitted with the paddle, beat the butter with the confectioners and granulated sugars until fluffy. Add the flour, espresso powder and salt and beat until just combined. Scrape the dough onto a work surface and pat into a disk. Wrap in plastic and refrigerate until just firm, about 30 minutes.

On a lightly floured work surface, roll out the dough 1/8 inch thick. Using a 2 1/2-inch round cookie cutter, stamp out cookies and transfer them to the prepared baking sheet. Sprinkle with turbinado sugar. Bake for 15 to 18 minutes, until the cookies are just firm to the touch and golden at the edges; rotate the baking sheet halfway through baking. Let the cookies cool on the baking sheet for 5 minutes, then transfer them to a rack to cool completely.